Synthesis and biological properties of new 5-nitroindazole derivatives

Bioorg Med Chem. 2005 May 2;13(9):3197-207. doi: 10.1016/j.bmc.2005.02.043.

Abstract

A series of new 3-alkoxy- or 3-hydroxy-1-[omega-(dialkylamino)alkyl]-5-nitroindazoles have been synthesized and their trichomonacidal, antichagasic and antineoplastic properties studied. Five derivatives (5, 6, 8, 9 and 17) showed remarkable trichomonacidal activity against Trichomonas vaginalis at 10 microg/mL concentration. Three compounds (8, 10, 11) exhibited interesting antichagasic activity and these same compounds moderate antineoplastic activity against TK-10 and HT-29 cell lines. Unspecific cytotoxicity against macrophages has also been evaluated and only compounds 9, 10 and 11 resulted cytotoxic at the higher dose evaluated (100 microg/mL), loosing cytotoxicity at lower doses. QSAR studies have been carried out. X-ray crystallographic study of compound 8 has been performed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Antitrichomonal Agents / chemical synthesis*
  • Antitrichomonal Agents / pharmacology
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Humans
  • Indazoles / chemical synthesis*
  • Indazoles / pharmacology
  • Models, Molecular
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Quantitative Structure-Activity Relationship
  • Trichomonas vaginalis / drug effects
  • Trypanocidal Agents / chemical synthesis*
  • Trypanocidal Agents / pharmacology
  • Trypanosoma cruzi / drug effects

Substances

  • Antineoplastic Agents
  • Antitrichomonal Agents
  • Indazoles
  • Trypanocidal Agents